CO.Cl.C(OCC)(=O)C.[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[CH2:26][CH2:25][N:24]([C:27](OC(C)(C)C)=[O:28])[CH2:23][C@H:22]1[O:34][CH3:35])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:36][CH2:37]C(Cl)=O>C(Cl)Cl.C(OCC)(=O)C>[Cl:36][CH2:37][C:27]([N:24]1[CH2:25][CH2:26][C@H:21]([NH:20][C:18](=[O:19])[O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:22]([O:34][CH3:35])[CH2:23]1)=[O:28]Methanol (10 ml), ethyl acetate (10 ml) and a 4 N hydrochloric acid/ethyl acetate solution (30 mL) were added to tert-butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained in Example (40a) (1.88 g, 5.16 mmol), and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, azeotropically dehydrated by adding toluene, and dissolved in methylene chloride (100 ml), followed by adding diisopropylethylamine (2.1 g). Chloroacetyl chloride (640 mg, 5.68 mmol) was dissolved in methylene chloride (50 ml), and the solution was added dropwise at 0° C. Following the dropwise addition, the mixture was stirred at 0° C. to room temperature overnight. The reaction solution was washed with water and aqueous sodium bicarbonate, concentrated under reduced pressure, and then azeotropically dehydrated by adding toluene to obtain the title compound. Half of the resulting compound was used for the next reaction without purification.
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